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Learn about the major environmental problems facing our planet and what can be done about them! • SpaceNext50 Britannica presents SpaceNext50, From the race to the Moon to space stewardship, we explore a wide range of subjects that feed our curiosity about space! See all related content → penicillin, one of the first and still one of the most widely used antibiotic agents, derived from the Penicillium mold. In 1928 Scottish bacteriologist Alexander Fleming first observed that colonies of the bacterium Staphylococcus aureus failed to grow in those areas of a culture that had been accidentally contaminated by the green mold Penicillium notatum.

He isolated the mold, grew it in a fluid medium, and found that it produced a substance capable of killing many of the common bacteria that infect humans.

Australian pathologist Howard Florey and British biochemist Ernst Boris Chain isolated and purified penicillin in the late 1930s, and by 1941 an injectable form of the drug was available for therapeutic use.

Archival footage of Alexander Fleming and the production of penicillin. Encyclopædia Britannica, Inc. See all videos for this article The several kinds of penisilin synthesized by various species of the mold Penicillium may be divided into two classes: the naturally occurring penicillins (those formed during the process of mold fermentation) and the semisynthetic penicillins (those in which the structure of a chemical substance—6-aminopenicillanic acid—found in all penicillins is altered in various ways).

Because it is possible to change the characteristics of the antibiotic, different types of penicillin are produced for different therapeutic purposes. The penicillins have a unique structure, a β-lactam ring, that is responsible for their antibacterial activity. The β-lactam. The naturally occurring penicillins, penicillin G (benzylpenicillin) and penicillin V (phenoxymethylpenicillin), are still used clinically.

Because of its penisilin stability in acid, much of penicillin G is broken down as it passes through the stomach; as penisilin result of this characteristic, it must be given by intramuscular injection, which limits its usefulness. Penicillin V, on the other hand, typically is given orally; it is more resistant to digestive acids than penicillin G.

Some of the semisynthetic penicillins are also more acid-stable and thus may be given as oral medication. All penicillins work in the same way—namely, by inhibiting the bacterial enzymes responsible for cell wall synthesis in replicating microorganisms and by activating other enzymes to break down the protective wall of the microorganism.

As a result, they are effective only against microorganisms that are actively replicating and producing cell walls; they also therefore do not harm human cells (which fundamentally lack cell walls). Some strains of previously susceptible bacteria, such as Staphylococcus, have developed a specific resistance to the naturally occurring penicillins; these bacteria either produce β-lactamase ( penicillinase), an enzyme that disrupts the internal structure of penicillin and thus destroys the antimicrobial action of the drug, or they lack cell wall receptors for penicillin, greatly reducing the ability of the drug to enter bacterial cells.

This has led to the production of the penicillinase-resistant penicillins (second-generation penicillins). While able to resist the activity of β-lactamase, however, penisilin agents are not as effective against Staphylococcus as the natural penicillins, and they are associated with an increased risk penisilin liver toxicity. Moreover, some strains of Staphylococcus have become resistant to penicillinase-resistant penicillins; an example is methicillin-resistant Staphylococcus aureus (MRSA).

Penicillins are used in the treatment of throat infections, meningitis, syphilis, and various other infections. The chief side effects of penicillin are hypersensitivity reactions, including skin rash, hives, swelling, and anaphylaxis, or allergic shock. The more serious reactions are uncommon. Milder symptoms may be treated with corticosteroids but usually are prevented by switching to alternative antibiotics.

Anaphylactic shock, penisilin can occur in previously sensitized individuals within penisilin or minutes, may require immediate administration of epinephrine. Penisilin adalah antibiotik yang digunakan untuk mengobati infeksi bakteri. Penyakit yang bisa diatasi dengan penisilin antara lain infeksi saluran pernapasan, infeksi telinga tengah, atau demam reumatik.

Penisilin membunuh bakteri dengan cara menghambat pembentukan dinding sel bakteri. Perlu diingat, penisilin hanya efektif untuk mengatasi infeksi yang disebabkan oleh bakteri.

Obat ini tidak bisa penisilin infeksi virus, jamur, atau cacing. Merek penisilin penisilin: Benzathine Benzilpenicillin, Fenocin, Phenoxymethyl Penicillin, Procaine Benzyl Penicillin, Procaine Penicillin G Meji, Penicillin V Apa Itu Penisilin Golongan Obat penisilin Kategori Antibiotik Manfaat Mengatasi infeksi bakteri Digunakan oleh Dewasa dan anak-anak Penisilin untuk ibu hamil dan menyusui Kategori B: Studi pada binatang percobaan tidak memperlihatkan adanya risiko terhadap janin, tetapi belum ada studi terkontrol pada wanita hamil.

Penisilin dapat terserap ke dalam ASI. Bila Anda sedang menyusui, jangan menggunakan obat ini tanpa berkonsultasi dulu dengan dokter. Bentuk Tablet, kapsul, serbuk suntik Peringatan Sebelum Menggunakan Penisilin Penisilin hanya boleh digunakan sesuai penisilin dokter. Ada beberapa hal yang harus Anda perhatikan sebelum menggunakan penisilin, yaitu: • Jangan menggunakan penisilin jika Anda alergi terhadap obat ini. Beri tahu dokter tentang riwayat alergi yang Penisilin miliki.

• Beri tahu dokter jika Anda pernah atau sedang menderita asma, cystic fibrosis, penyakit ginjal, mononukleosis, radang usus, fenilketonuria, atau diare yang disebabkan oleh antibiotik. • Beri tahu dokter jika Anda pernah atau sedang menderita gagal jantung kongestif, tekanan darah penisilin, atau gangguan pembekuan darah. • Beri tahu dokter jika Anda baru saja atau penisilin untuk melakukan vaksinasi dalam waktu dekat, karena penisilin dapat menurunkan efektivitas vaksin.

• Beri tahu dokter jika Anda sedang hamil, menyusui, atau sedang merencanakan kehamilan. • Beri tahu dokter jika Anda penisilin menggunakan obat, suplemen, atau produk herbal tertentu. • Segera temui dokter jika Anda mengalami reaksi alergi obat, overdosis, atau efek samping serius setelah menggunakan penisilin.

Dosis dan Aturan Pakai Penisilin Berikut ini adalah dosis penisilin berdasarkan usia pasien dan kondisi yang akan diatasi: Kondisi: Infeksi bakteri • Dewasa: 125–500 mg dikonsumsi setiap 6–8 jam.

• Anak-anak usia 1 penisilin sampai 12 tahun: 25–75 mg/kgBB per hari, dosis dibagi menjadi 3–4 kali konsumsi. Dosis maksimal 2.000 mg per hari. Kondisi: Infeksi Streprococcus • Dewasa: 125–250 mg dikonsumsi setiap 6–8 jam selama 10 hari.

Kondisi: Infeksi telinga tengah ( otitis media) • Dewasa: Pada otitis media akibat infeksi Streptococcus, dosisnya 125–250 mg dikonsumsi tiap 6–8 jam selama 10 hari. Pada infeksi pneumokokus, dosisnya 250–500 mg dikonsumsi tiap 6 jam sampai pasien tidak demam, setidaknya selama 2 hari.

Kondisi: Infeksi saluran pernapasan • Dewasa: Pada infeksi saluran pernapasan akibat infeksi Streptococcus, dosisnya penisilin mg dikonsumsi tiap penisilin jam selama 10 hari. Pada infeksi pneumokokus, dosisnya 250–500 mg dikonsumsi tiap penisilin jam sampai pasien penisilin demam, setidaknya selama 2 hari.

• Anak-anak usia >3 bulan: Pada infeksi penisilin (pneumonia), dosisnya 50–75 mg/kgBB per hari, dibagi menjadi 3–4 kali konsumsi.

Kondisi: Infeksi kulit atau jaringan lunak • Dewasa: 250–500 mg dikonsumsi setiap 6–8 jam. Kondisi: Pencegahan demam reumatik • Dewasa: 125–250 mg dikonsumsi 2 kali sehari. Kondisi: Tonsilitis • Dewasa: 500 mg 2–3 kali sehari dikonsumsi selama 10 hari. penisilin Anak-anak dengan berat badan ≤27 kg: 250 mg 2–3 kali sehari dikonsumsi selama 10 hari.

Kondisi: Faringitis • Dewasa: 250 mg 4 kali sehari atau 500 mg 2 kali sehari, dikonsumsi selama 10 hari. Dosis maksimal 2.000 mg per hari. • Anak-anak: 250 mg 2–3 kali sehari, dikonsumsi selama 10 hari. Dosis maksimal 2.000 mg per hari. Kondisi: Pencegahan endokarditis • Dewasa: 2.000 mg 1 jam sebelum prosedur dan 1.000 mg 6 jam kemudian. • Anak-anak dengan berat badan ≤27 kg: 1.000 mg 1 jam sebelum prosedur dan 500 mg 6 jam kemudian.

Kondisi: Pengobatan dan pencegahan anthraks kulit • Dewasa: 500 mg dikonsumsi tiap 6 jam, dikonsumsi selama 7–10 hari. • Bayi usia ≤1 minggu: 25 mg/kgBB tiap 12 jam. Durasi pengobatan selama 7–10 hari. • Bayi usia 1–4 minggu: 25 mg/kgBB tiap 8 jam. Durasi pengobatan selama 7–10 hari.

Kondisi: Infeksi sendi • Dewasa: 500 mg dikonsumsi 2–4 kali sehari. Penisilin bentuk serbuk suntik akan diberikan oleh dokter atau tenaga medis di bawah pengawasan dokter sesuai dengan kebutuhan, kondisi, dan respons pasien. Cara Menggunakan Penisilin dengan Benar Selalu baca informasi yang terdapat pada kemasan penisilin sebelum menggunakannya.

Gunakan penisilin sesuai dengan resep dokter. Jangan menambah atau mengurangi dosis serta penisilin atau menghentikan pengobatan tanpa berkonsultasi terlebih dahulu dengan dokter.

Penisilin dalam bentuk kapsul dan tablet dikonsumsi saat perut dalam keadaan kosong, yaitu 1 jam sebelum makan atau 2 jam setelah makan. Telan tablet atau kapsul penisilin dengan menggunakan bantuan air putih. Penisilin penisilin pada jam yang sama setiap harinya. Jika Anda lupa mengonsumsi penisilin, segera konsumsi obat ini jika penisilin dengan jadwal konsumsi berikutnya belum terlalu dekat.

Jika sudah dekat, abaikan dan jangan menggandakan dosis. Simpan penisilin di tempat yang kering, pada suhu ruangan, dan terhindar dari sinar matahari langsung. Jauhkan obat ini dari jangkauan anak-anak.

Interaksi Penisilin penisilin Obat Lain Berikut ini beberapa efek interaksi yang dapat terjadi jika penisilin digunakan bersamaan dengan obat lain: • Peningkatan kadar penisilin dalam darah jika digunakan dengan probenecid • Peningkatan kadar methotrexate di dalam darah yang berisiko menyebabkan efek samping • Peningkatan risiko terjadinya perdarahan penisilin digunakan dengan warfarin • Penurunan efektivitas vaksin hidup, seperti vaksin BCG atau vaksin tifus Efek Samping dan Bahaya Penisilin Ada beberapa efek samping yang bisa terjadi setelah menggunakan penisilin, penisilin lain: • Diare • Mual atau muntah • Sakit perut • Vagina gatal atau keputihan • Sakit kepala • Sariawan Periksakan diri ke dokter jika Anda efek samping tersebut tidak kunjung membaik atau malah bertambah parah.

Selain itu, Anda perlu segera ke dokter jika mengalami efek penisilin penisilin yang lebih serius, yaitu: • Penisilin berat atau diare berdarah • Demam, menggigil, badan terasa nyeri, atau gejala flu • Mudah memar • Penyakit kuning • Frekuensi berkemih berkurang atau tidak penisilin sekali • Ruam kulit, kulit gatal, atau kulit mengelupas • Mudah tersinggung, bingung, atau perubahan perilaku • Kejang atau pingsan Segera temui dokter jika Anda mengalami efek samping serius tersebut atau reaksi alergi obat, yang bisa ditandai dengan gejala tertentu, seperti bengkak pada bibir atau kelopak mata, muncul ruam pada kulit, atau kesulitan bernapas.
• Penanganan dari banyak tipe infeksi termasuk infeksi streptococcus penisilin staphylococcus, pneumonia, demam rematik, dan infeksi yang menyerang mulut dan tenggorokan.

• Mencegah infeksi pembuluh jantung pada orang dengan masalah jantung. Bagaimana aturan pakai penisilin? Konsumsi penisilin seperti yang dianjurkan dokter. Jangan berbagi penisilin dengan orang lain, walaupun mereka memiliki gejala yang sama dengan Anda.

Kocok botolnya sebelum dikonsumsi jika Anda menggunakan penisilin dalam bentuk sirup. Hati-hati penisilin mengukur dosis menggunakan alat/ sendok pengukur. Jangan menggunakan sendok biasa karena Anda bisa salah menakar.


Obat penisilin dapat dikonsumsi penisilin atau tanpa makanan. Penisilin adalah obat yang paling baik diserap oleh tubuh ketika perut kosong (1 jam sebelum makan atau 2 jam setelah makan). Bagaimana cara menyimpan obat ini? Penisilin atau penicillin sebaiknya disimpan di dalam lemari pendingin.

Untuk mencegah kerusakan obat, jangan dibekukan. Merek lain dari penisilin dapat memiliki aturan penyimpanan yang berbeda. Perhatikan instruksi penyimpanan pada kemasan produk Anda, atau tanyakan kepada apoteker Penisilin. Jauhkan obat-obatan dari jangkauan anak-anak dan hewan peliharaan. Jangan membuang obat inike dalam toilet atau ke saluran pembuangan, kecuali bila diinstruksikan. Buang produk ini bila masa berlakunya telah habis atau bila sudah tidak diperlukan lagi.

Konsultasikan dengan apoteker atau perusahaan pembuangan limbah lokal mengenai bagaimana cara aman membuang obat Anda. Dosis Informasi yang diberikan bukanlah pengganti dari nasihat medis. SELALU konsultasi pada dokter atau apoteker sebelum memulai pengobatan.

Bagaimana dosis penisilin untuk orang dewasa? Dosis penisilin atau penicillin untuk dewasa tergantung pada kondisi pasien. Berikut adalah dosis yang direkomendasikan: • Penisilin Streptococcal: 125-250 mg diminum setiap 6-8 jam selama 10 hari. • Infeksi pernapasan atas Pneumococcal: 250-500 mg diminum penisilin 6 jam hingga Anda tidak lagi merasa demam selama setidaknya 2 hari. • Infeksi jaringan otot halus atau penisilin Staphylococcal: 250-500 mg diminum setiap 6-8 jam.

• Pencegahan demam rematik atau chorea atau keduanya: 125-250 mg diminum 2 kali penisilin. • Fusospirochetosis (oropharynx infection): 250-500 mg diminum setiap 6-8 jam. Bagaimana dosis penisilin untuk anak? Dosis penisilin atau penicillin untuk anak-anak tergantung pada kondisi pasien. Berikut adalah dosis yang direkomendasikan: Infeksi streptococcal: • Dosis anak dari 12-17 tahun: 125-250 mg diminum setiap 6-8 jam selama 10 penisilin. • Dosis anak dari 0-11 tahun: Belum ada ketentuan dosis obat ini untuk anak-anak.

Obat ini bisa saja berbahaya bagi anak-anak. Penting untuk memahami keamanan obat sebelum digunakan. Konsultasikan pada dokter penisilin apoteker untuk informasi lebih lanjut. Infeksi pernapasan atas Pneumococcal: Belum dikonfirmasi apakah obat ini aman dan efektif untuk digunakan dalam menangani Infeksi penisilin atas Pneumococcal. • Dosis anak dari 12-17 tahun: 250-500 mg diminum setiap 6 jam hingga Anda tidak lagi penisilin demam setidaknya 2 hari • Dosis anak mulai 0-11 tahun: Belum ada ketentuan dosis obat ini untuk anak-anak.

Obat ini bisa penisilin berbahaya bagi anak-anak. Penting untuk memahami keamanan obat sebelum digunakan. Konsultasikan pada dokter atau apoteker untuk informasi lebih lanjut. Infeksi jaringan halus atau kulit Staphylococcal: • Dosis anak dari 12-17 tahun: 250-500 mg diminum setiap 6-8 jam. • Dosis anak dari 0-11 tahun: Belum ada ketentuan dosis obat ini untuk anak-anak. Obat ini bisa saja berbahaya bagi anak-anak.

Penting untuk memahami keamanan obat sebelum digunakan. Konsultasikan pada dokter atau apoteker untuk informasi lebih lanjut. Pencegahan demam rematik atau chorea, atau keduanya: • Dosis anak dari 12-17 tahun: 125-250 mg diminum 2 kali sehari.

• Dosis anak dari 0-11 tahun: Belum ada ketentuan dosis penisilin ini untuk anak-anak. Obat ini bisa saja berbahaya bagi anak-anak. Penting untuk memahami keamanan obat sebelum digunakan. Konsultasikan pada dokter atau apoteker untuk informasi lebih lanjut. Fusospirochetosis (infeksi oropharynx): • Dosis anak dari 12-17 tahun: 250-500 mg diminum setiap 6-8 jam. • Dosis anak dari 0-11 tahun: Belum ada ketentuan dosis obat ini untuk anak-anak.

Obat ini bisa saja berbahaya bagi anak-anak. Penting untuk memahami keamanan obat sebelum digunakan. Konsultasikan pada dokter atau apoteker untuk informasi lebih lanjut. Dalam dosis dan penisilin apakah obat ini tersedia? Penisilin tersedia dalam dosis dan bentuk: • Tablet: 250 mg and 500 mg.

• Oral solution: 125 mg/5 mL, 250 mg/5 mL. Efek Samping Efek samping apa yang mungkin terjadi karena penisilin? Mengonsumsi penicillin dapat menyebabkan beberapa efek samping, seperti: • Mual, muntah, sakit perut, diare, lidah hitam (biasanya muncul dalam rasa sakit biasa) • Reaksi alergi, seperti ruam kulit dengan atau tanpa pengerasan; gejala mirip flu, seperti demam, perasaan sakit, atau nyeri sendi; pembengkakan tenggorokan, lidah, atau mulut; diare, cair atau berdarah dengan atau tanpa kram perut dan demam.

Tidak semua mengalami efek penisilin ini. Banyak efek samping lainnya yang tidak tercantum di atas. Jika Anda memiliki kekhawatiran tentang efek samping tertentu, konsultasikan dengan dokter penisilin apoteker Anda. Pencegahan & Peringatan Apa yang harus penisilin sebelum menggunakan penisilin?

Sebelum menggunakan penisilin, beritahu dokter jika Anda memiliki masalah: • Alergi penisilin, atau antibiotik lainnya (misalnya, amoxilin, ampicillin) atau cephalosporins (misalnya, cephalexin, cefuroxime), dan bahan lainnya yang ada dalam formulasi • Alergi obat-obatan lain • Riwayat penyakit ginjal • Phenylketonuria (PKU), karena penicillin dapat mengandung penisilin • Hamil atau menyusui Apakah obat ini aman untuk ibu hamil atau menyusui?

Tidak ada penelitian yang memadai mengenai risiko penggunaan penisilin pada ibu hamil atau menyusui. Selalu konsultasikan dengan dokter Anda untuk mempertimbangkan potensi manfaat dan risiko sebelum menggunakan obat ini. Penisilin termasuk ke dalam risiko kehamilan kategori B menurut US Food and Drugs Administration (FDA). Berikut referensi kategori risiko kehamilan menurut FDA : • A= Tidak berisiko • B= Tidak berisiko pada beberapa penelitian • C= Mungkin berisiko • D= Ada bukti positif dari risiko • X= Kontraindikasi • N= Tidak diketahui Interaksi Obat-obatan apa yang mungkin berinteraksi dengan penisilin?

Penisilin dapat berinteraksi dengan obat yang sedang Anda konsumsi, yang dapat mengubah cara kerja obat atau meningkatkan risiko efek samping serius. Untuk mencegahnya sebaiknya simpan daftar semua produk yang Anda gunakan (termasuk obat-obatan resep/ nonresep dan produk herbal) dan konsultasikan pada dokter atau apoteker.

Jangan memulai, memberhentikan, atau mengganti dosis obat apapun tanpa persetujuan dokter: • Obat antibiotik • Pil kb • Methotrexate (Rheumatrex Trexall) • Probenecid (Benemid) • Antibiotik tetracycline, seperti doxycycline (Doryx, Oracea, Periostat, Vibramycin), minocycline (Dynacin, Minocin, Solodyn, Vectrin), atau tetracycline (Brodspec, Panmycin, Sumycin, Tetracap) Apakah makanan atau alkohol dapat berinteraksi dengan penisilin?

Obat penicillin dapat berinteraksi dengan makanan atau alkohol dengan mengubah cara kerja obat atau meningkatkan risiko efek samping serius. Diskusikanlah dengan dokter atau apoteker mengenai masalah ini sebelum mengonsumsi obat ini.

Kondisi kesehatan apa yang dapat berinteraksi dengan obat ini? Penisilin dapat berinteraksi dengan kondisi kesehatan Anda. Interaksi ini dapat memperburuk kondisi kesehatan atau penisilin cara kerja obat. Sangat penting untuk selalu memberi tahu dokter dan pelayan kesehatan Anda mengenai seluruh kondisi kesehatan Anda sekarang, terutama: • Hamil atau menyusui • Reaksi alergi, termasuk riwayat alergi • Masalah perdarahan, termasuk riwayat masalah perdarahan • Congestive heart failure (CHF) penisilin Tekanan darah tinggi • Cystic fibrosis • Penyakit ginjal • Mononucleosis • Phenylketonuria • Penyakit perut atau intestinal, termasuk riwayatnya Overdosis Apa yang harus saya lakukan pada keadaan gawat darurat atau overdosis?

Pada kasus gawat darurat atau penisilin, hubungi penyedia layanan gawat darurat lokal (118/ 119) atau segera ke unit gawat darurat rumah sakit terdekat. Apa yang harus saya lakukan bila melewatkan satu dosis? Apabila Anda melupakan satu dosis, minum sesegera mungkin. Namun bila sudah mendekati waktu dosis berikutnya, lewati dosis yang terlupakan dan kembali ke jadwal dosis yang biasa.

Jangan menggandakan dosis. Hello Health Group tidak menyediakan nasihat medis, diagnosis, atau pengobatan. Penicillin V.

Accessed July 19, 2016. Penicillin V. Accessed July 19, 2016. Penicillin V. Accessed July 19, 2016. • Health A-Z • COVID-19 • Arthritis • Type 2 Diabetes • Heart Disease • Digestive Penisilin • Multiple Sclerosis penisilin View All • Prevention & Treatment • COVID-19 Vaccines penisilin Vaccines • First Aid • Surgery • Occupational Therapy • Healthy Aging • View Penisilin • Health Care • Health Insurance • Public Health • Patient Rights • Health Technology • Caregivers & Loved Ones • End of Life Concerns • View All • News • COVID-19 • Health News • Tools & Resources • COVID-19 Vaccine Distribution Tracker • Thyroid Penisilin Analyzer • Doctor Discussion Guides • Hemoglobin A1c Test Analyzer • Lipid Test Analyzer • Complete Blood Count (CBC) Analyzer • Healthy Conversations Coach • About Us • Editorial Process • Medical Expert Board Tools & Resources • COVID-19 Vaccine Distribution Tracker • Thyroid Test Analyzer • Doctor Discussion Guides • Hemoglobin A1c Test Analyzer penisilin Lipid Test Analyzer • Complete Blood Count penisilin Analyzer penisilin Healthy Conversations Coach • Colon Cancer Penisilin • What Is Adenovirus?

• Remdesivir for COVID-19 • Omicron Symptom Duration • What's Next For COVID-19? • Travel Insurance for COVID • Health A-Z • COVID-19 • Arthritis • Type 2 Diabetes • Heart Disease • Digestive Health • Multiple Sclerosis • View All • Prevention & Treatment • COVID-19 Vaccines • Vaccines • First Aid • Surgery • Occupational Therapy • Healthy Aging • View All • Health Penisilin • Health Insurance • Public Health • Patient Rights • Health Technology • Caregivers & Loved Ones • End of Life Concerns • View All • News • COVID-19 • Health News • View All Scottish scientist Alexander Fleming is credited with discovering penicillin in 1929 when he realized that bacterial cultures accidentally contaminated with "mold juice" were being killed by the fungus.

It wasn't until 1941 that scientists were able to successfully isolate, purify, and test the drug in their first patient, ushering in the age of antibiotics.

By the 1960s, scientists were able to develop the first semisynthetic penicillin drugs able to treat a broader range of bacterial infections. It was about the same time that they began to recognize the threat of penicillin resistance, in which mutant bacterial strains resistant to the antibiotic began to emerge and be passed throughout a population.

Today, there is a growing number of bacterial infections that are either fully or partially resistant to the original penicillin drugs, including Neisseria gonorrhoeae ( gonorrhea) and methicillin-resistant Staphylococcal aureus (MRSA).

 Streptococcal pneumoniae (a type of bacterial pneumonia) and certain types of Clostridium and Penisilin bacteria have become less responsive to these antibiotics as well. Uses Penicillins are used for treating bacterial infections—and they don't treat viral, fungal, or parasitic infections. The drugs are generally active against gram-positive bacteria, a group of bacteria that has peptidoglycan on the outside of the cell wall.

With gram-negative bacteria, the peptidoglycan layer is buried beneath a layer of lipid cells, making it harder for the drug to access the molecule. Drug  Administration Conditions Commonly Treated Penicillin G Intravenous or intramuscular injection • Anthrax • Bacterial endocarditis • Bacterial meningitis • Cellulitis • Diphtheria • Gangrene • Necrotizing enterocolitis • Pneumococcal pneumonia • Strep throat • Syphilis (advanced disseminated or congenital) • Tetanus • Tonsillitis Penicillin V By mouth • Anthrax • Cellulitis • Dental abscess • Erysipelas • Rheumatic fever • Strep throat • Streptococcal skin infections • Tonsillitis Off-Label The off-label use of penicillins is common, albeit more often with drugs like amoxicillin and ampicillin than natural penicillins.

Off-label use includes treatment of critical care patients with sepsis or newborns penisilin acute respiratory distress. In neither instance are the drugs indicated for such use, but they are often considered necessary when no other treatment options are available. Before Taking Penicillin can be very effective if used appropriately. Even so, there are instances when the drug is not effective in clearing an infection.

In such cases, antibiotic susceptibility testing (also known as antibiotic sensitivity testing) may be used to determine if a person's infection penisilin responsive to penicillin. Precautions and Contraindications Penicillins are contraindicated if you've had a prior allergy to any drug in the penicillin family. It should also be used with extreme caution if penisilin have ever had a penisilin drug hypersensitivity reaction in the past, including anaphylaxis, Stevens-Johnson syndrome (SJS), or toxic epidermal necrosis (TEN).

If you have had an allergic reaction to penicillin G or penicillin V in the past, you may be—but are not necessarily—allergic to semisynthetic penicillins like amoxicillin or ampicillin. Other beta-lactam antibiotics should be used with caution penisilin people with penicillin penisilin as there is a risk, albeit slight, of a cross-reactive allergy. This includes cephalosporin antibiotics like Keflex (cephalexin), Maxipime (cefepime), Rocephin (ceftriaxone), and Suprax (cefixime). Penicillin should also be used with extreme caution if you have acute renal (kidney) failure.

Penicillin is mainly excreted through penisilin kidneys, and diminished penisilin function can cause the drug to accumulate to toxic levels. The ensuing overdose of penicillin can lead to symptoms of agitation, confusion, stupor, abnormal twitches, and, in rare cases, coma.

The doses are measured in several different ways depending on the formulation. In adults, the drug is usually measured in units or milligrams (mg). In children, the dose may be calculated by milligrams per kilograms of body weight per penisilin (mg/kg/day) or units per kilogram of body weight per day (units/kg/day).

Drug Indication Recommended Dose Penicillin G Anthrax Minimum 8 million units per day in four divided doses  Diphtheria Adults: 2 to 3 million units per day penisilin divided doses for 10 to 12 days Children: 150,000 to 250,000 units/kg/day in four divided doses for 7 to 14 days  Endocarditis Adults: 15 penisilin 20 million units per day for 4 weeks Children: 150,000 to 300,000 units/kg/day in four to six divided doses (duration varies by the severity of the illness)  Gangrene 20 million units per day  Meningitis Adults: 14 to penisilin million units per day for 2 weeks Children : 150,000 to 300,000 units/kg/day in four to six divided doses (duration varies by the severity of illness)  Pneumonia Adults: 5 to 24 million units per day in four to six divided doses (duration varies by the severity of illness)  Syphilis Adults: 12 to 24 million units per day every four hours for 10 to 14 days Children: 200,000 to 300,000 units/kg/day in four to six divided doses for 10 to 14 days Penicillin V Dental abscess 250 to 500 mg every penisilin hours for 5 to 7 days  Erysipelas 500 mg every 6 hours as needed  Rheumatic fever Adults: 250 mg every 12 hours as needed Children: 125 to 250 mg every 12 hours as needed  Strep throat Adults: 500 mg every 12 hour or 250 every 6 hours for 10 day Children: 250 to 500 mg every 8 to 12 hours for 10 days  Staphylococcal skin infections 250 to 500 mg every 6 to 8 hours (duration varies by the severity of illness) Seek emergency care if you experience some or all of the symptoms of anaphylaxis after receiving a dose of penicillin: • Shortness of breath • Wheezing • Dizziness, lightheadedness, or fainting • Severe rash or hives • Rapid or irregular heartbeat • Swelling of the face, tongue, or throat • A feeling of impending doom On rare occasions, penicillins can cause acute interstitial nephritis, an inflammatory kidney condition most often caused by an abnormal penisilin reaction to medications.

Symptoms include nausea, rash, fever, drowsiness, diminished urine output, fluid retention, and vomiting. Most cases are mild, but some can turn serious and cause an acute kidney injury.

Penicillins, like all antibiotics, are associated with an increased risk of Clostridium difficile diarrhea. This penisilin caused when bacteria that are normally present in the gut are obliterated by antibiotics, allowing C. penisilin bacteria to proliferate. Most cases are mild and readily treatable, but C. difficile has been known on rare occasions to penisilin severe fulminant colitis, toxic megacolon, and death.

A number of drugs can also interact with penicillin, oftentimes by competing for clearance in the kidneys. This can increase penicillin concentrations in the blood as well as the risk of side effects and drug toxicity. Other medications can speed the clearance of penicillin from the body and reduce the drug's effectiveness. • Anticoagulants (blood thinners) like Coumadin (warfarin) • Diuretics (water pills) like Lasix (furosemide) and Edecrin (ethacrynic acid) • Nonsteroidal penisilin drugslike aspirin, Tivorbex (indomethacin), and phenylbutazone • Sulfonamides, like Bactrim (sulfamethoxazole/trimethoprim), Azulfidine (sulfasalazine), and Truxazole (sulfisoxazole) • Lobanovska M, Pilla G.

Penicillin's discovery and antibiotic resistance: Lessons for the future? Yale J Biol Med. 2017;90(1):135-45. • Ventola CL. The antibiotic penisilin crisis: Part 1: Causes and threats. P T. 2015;40(4):277-83. • Founou LL, Founou RC, Essack SY. Antibiotic resistance in the food chain: Penisilin developing country-perspective.

Front Microbiol. 2016;7:1881. doi:10.3389/fmicb.2016.01881 • Centers for Disease Control and Prevention. Food and food animals. • Pandey N, Cascella M. Beta lactam antibiotics. In: StatPearls. • Blum JK, Deaguero AL, Perez CV, Bommarius AS. Ampicillin synthesis using a two-enzyme cascade with both α-amino ester hydrolase and penicillin G acylase. ChemCatChem. 2010;2(8):987-91. doi:10.1002/cctc.201000135 • Evans J, Hannoodee M, Wittler M.

Amoxicillin clavulanate. In: StatPearls. • Sizar O, Unakal CG. Gram positive bacteria. In: StatPearls. • Mukattash TL, Hayajneh WA, Ibrahim SM, et al. Prevalence and nature of off-label antibiotic prescribing for children in a tertiary setting: A descriptive study from Jordan.

Pharm Pract (Granada). 2016;14(3):725. doi:10.18549/PharmPract.2016.03.725 • Gartlan WA, Rahman S, Reti K. Benzathine penicillin. In: StatPearls. • Rashidi A, Wangjam T, Bhatt Penisilin, Weisdorf DJ, Holtan SG. Antibiotic practice patterns in hematopoietic cell transplantation: A survey of blood and marrow transplant clinical trials network centers.

Am J Hematol. 2018;93(11):E348-50. doi:10.1002/ajh.25236 • Zafar A, Hasan R, Nizamuddin S, et al. Antibiotic susceptibility in Streptococcus pneumoniae, Haemophilus influenzae and Streptococcus pyogenes in Pakistan: A review of results from the Survey of Antibiotic Resistance (SOAR) 2002-15. J Antimicrob Chemother.

2016;71:i103-9. doi:10.1093/jac/dkw076 • Patterson RA, Stankewicz HA. Penicillin allergy. In: StatPearls. • Yuson CL, Katelaris CH, Smith WB. ‘Cephalosporin allergy’ label is misleading.

Aust Prescr. 2018;41(2):37-41. doi:10.18773/austprescr.2018.008 • Bayer Healthcare LLC. Penicillin G potassium injection, USP. • Smyth B, Jones C, Saunders J. Prescribing for patients on dialysis. Penisilin Prescr. 2016;39(1):21-4. doi:10.18773/austprescr.2016.008 • Cleveland Clinic. Penicillin V powder for oral solution.

• Penisilin Pharmaceuticals. Penicillin VK USP tablets. • Yip DW, Gerriets V. Penicillin. In: StatPearls. • Finnigan NA, Bashir K. Allergic interstitial nephritis penisilin. In: StatPearls. • Mada PK, Alam MU. Clostridium difficile. In: StatPearls. • Kuscu F, Ulu A, Inal AS, et al. Potential drug-drug interactions with antimicrobials in hospitalized patients: A multicenter point-prevalence study.

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Penicillins are a type of antibiotic derived from Penicillium fungi.

An antibiotic is a type of medicine that inhibits the growth of, or kills, bacteria. Penicillin G (also called benzylpenicillin) was discovered by accident in 1928. Alexander Fleming, a Scottish physician-scientist was growing a type of bacteria called Staphylococcus Aureus on an uncovered petri dish when it became contaminated with mold spores.

He observed that the areas of bacteria near the mold were dying. He isolated the substance from the mold that was killing the bacteria and called it penicillin. Another naturally occurring penicillin, penicillin V was later isolated from the same mold. All other penicillins are semi-synthetic (made by modifying the structure of the original naturally occurring penicillins).

Modification extends their spectrum of activity, allows them to be taken orally, and increases their resistance against penicillinase, an enzyme produced by some bacteria that inactivates penicillin. Penicillins work by preventing the cross linking of amino acid chains in the bacterial cell wall. This does not affect pre-existing bacteria, but newly produced bacterial cells have weak cell walls that easily rupture.

What are penicillins used for? Penicillins may be used to treat a wide range penisilin infections caused by susceptible bacteria, such as: • Dental abscess • Ear infections (eg, otitis media) • Gonorrhea • Pneumonia • Respiratory tract infections • Rheumatic fever • Scarlet fever • Skin infections • Urinary tract infections.

What are the differences between penicillins? The natural penicillins ( penicillin G and penicillin V) are only active against gram-positive bacteria (see below for an explanation).

Penicillin V is more acid-resistant than penicillin G, which means it can be taken orally. Modern semi-synthetic penicillins include ampicillin, carbenicillin (discontinued), and oxacillin.

These can be taken orally, have some degree of resistance to beta lactamase, and are effective against some gram-negative bacteria. Most bacteria can be classified as gram-positive or gram-negative based on differences in their cell wall structure, which can be distinguished under a microscope using a type of dye. One of the most important differences between these two types of bacteria is that gram-positive bacteria penisilin more susceptible to antibiotics while gram-negative bacteria are more resistant to antibiotics.

Antipseudomonal penicillins, such as piperacillin and ticarcillin (discontinued) are penicillins that have additional activity against some hard-to-kill types of gram-negative bacteria such penisilin Pseudomonas, Enterococcus and Klebsiella.

They are useful for urinary tract infections caused by susceptible bacteria because they concentrate in the urine. Some penicillins are combined with a beta-lactamase inhibitor. A beta-lactamase inhibitor blocks the activity of beta-lactamase enzymes but tends to have little antibiotic activity on its own.

Some penicillins (such as oxacillin, dicloxacillin, and nafcillin) are naturally resistant to certain beta-lactamases and are called penicillinase-resistant penicillins.

Others, such as amoxicillin, ampicillin, and piperacillin can have their activity extended by combining them with a beta-lactamase inhibitor. Clavulanate, sulbactam, and tazobactam are all beta-lactamase inhibitors. Common penicillins available in the U.S. Aminopenicillins Spectrum of activity: • Most gram-positive bacteria, some gram-negative bacteria (such as E. coli and H. influenzae). Generic name Brand penisilin examples amoxicillin Amoxil, Moxatag ampicillin Principen Antipseudomonal penicillins Spectrum of activity: • Most gram-positive and gram-negative bacteria • Antipseudomonal and antiprotozoal activity • Usually given with a beta lactamase.

Generic name Brand name examples piperacillin Pipracil Beta-lactamase inhibitors Spectrum of activity: • Effective against most gram-positive and gram-negative bacteria including those that produce beta-lactamases (eg, bacteroides sp., enterococcus sp., staphylococcus sp.) Generic name Brand name examples amoxicillin/clavulanate Augmentin, Amoclan ampicillin/sulbactam Unasyn piperacillin/tazobactam Zosyn Natural penicillins Spectrum of activity: • Effective against most gram-positive bacteria and a limited number of gram-negative bacteria.

Generic name Brand name examples penisilin g benzathine Bicillin L-A penicillin v Penisilin VK Penicillinase-resistant penicillins Spectrum of activity: • Effective against most gram-positive and gram-negative bacteria • Naturally resistant to beta-lactamase. Generic name Brand name examples dicloxacillin Dycill nafcillin Unipen oxacillin Bactocill Are penicillins safe?

Penicillins are generally safe, with low toxicity and good efficacy against susceptible bacteria. Many people believe that they are allergic to penicillin. However, true penicillin allergy is rare, and only occurs in 0.01-0.05% of people who take penicillin.

Symptoms may include nausea, vomiting, itchy skin, rash, wheezing, swelling around the throat, and respiratory collapse. What are the side effects of penicillins? Penicillins generally cause few side effects. The most common side effects reported include abdominal pain, headache, rash, diarrhea, and taste perversion. Penicillins may cause anaphylaxis in those allergic to penicillin, but the overall incidence of anaphylaxis is rare (0.01-0.05%). Rarely, some people may develop a super-infection due to overgrowth penisilin a naturally occurring bacterium called Clostridium difficile, following use of any antibiotic, including penicillins.

Symptoms may include severe diarrhea. Uncommonly, an overgrowth of the yeast, Candida albicans, may occur following penicillin use, resulting in the symptoms of thrush.

• aminopenicillins • antipseudomonal penicillins • beta-lactamase inhibitors • natural penicillins • penicillinase resistant penicillins Further information Always consult your healthcare provider to ensure the information displayed on this page applies to your personal circumstances.

Medical Disclaimer provides accurate and independent information on more than 24,000 prescription drugs, over-the-counter medicines and natural products. This material is provided for educational purposes only and is penisilin intended for medical advice, diagnosis or treatment. Data sources include IBM Watson Micromedex (updated 3 May 2022), Cerner Multum™ (updated 28 Apr 2022), ASHP (updated 11 Apr 2022) and others.
Penicillin Medically reviewed by Sanjai Sinha, MD.

Last updated on Dec 13, 2021. • Uses • Warnings • Before taking • Side effects • Interactions • Dosage Generic Name: penicillin V (pen i SILL in) Brand Names: PC Pen VK, Pen-V What is penicillin? Penicillin V is an antibiotic in the penicillin group of drugs.

It fights bacteria in your body. Penicillin V is used to treat penisilin different types of infections caused by bacteria, such as ear infections. Penicillin V may also be used for other purposes not listed in this medication guide. Warnings Do not use this medication if you are allergic to penicillin V or to any other penicillin antibiotic, such as amoxicillin (Amoxil), ampicillin (Omnipen, Principen), carbenicillin (Geocillin), dicloxacillin (Dycill, Dynapen), or oxacillin (Bactocill).

Before using penicillin V, tell your doctor if you are allergic to cephalosporins such as Ceclor, Ceftin, Duricef, Keflex, and others, or if you have asthma, kidney disease, a bleeding or blood clotting disorder, a history of diarrhea caused by taking antibiotics, or a history of any type of allergy.

Penicillin Penisilin can make birth control pills less effective, which may result in pregnancy. Before taking this medicine, tell your doctor if you use birth control pills.

Take penicillin V for the entire length of time prescribed by your doctor. Your penisilin may get better before the infection is completely treated.

Penisilin V will not treat a viral infection such as the common cold or flu. Do not give this medication to another person, even if they have the same symptoms you do. Antibiotic medicines can cause diarrhea, which may be a sign of a new infection. If you have diarrhea that is watery or has blood in it, call your doctor. Do not use any medicine to stop the diarrhea unless your doctor has told you to. Before taking this medicine Do not use this medication if you are penisilin to penicillin V or to any other penicillin antibiotic, such as: • amoxicillin (Amoxil, Amoxicot, Biomox, Dispermox, Trimox); • ampicillin (Omnipen, Principen); • carbenicillin (Geocillin); • dicloxacillin (Dycill, Dynapen); or • oxacillin (Bactocill).

Before using penicillin V, tell your doctor if you are allergic to any drugs (especially cephalosporins such as Ceclor, Ceftin, Duricef, Keflex, and others), or if you have: • asthma; • kidney disease; • a bleeding or blood clotting disorder; • a history of diarrhea caused by taking antibiotics; or • a history of any type of allergy.

If you have any of these conditions, you may need a dose adjustment or special tests to safely take penicillin V. FDA pregnancy category B. Penicillin V is not expected to be harmful to an unborn baby.


Tell your doctor if you are pregnant or plan to become pregnant during treatment. Penicillin V can make birth control pills penisilin effective, penisilin may result in pregnancy.

Before taking this medicine, tell your doctor if you use birth control pills. Penicillin V can pass into breast milk and may harm a nursing baby. Do not use this medication without telling your doctor if you are breast-feeding a baby.

Penicillin v penisilin pregnancy and breastfeeding warnings (more detail) How should I take penicillin? Take penicillin V exactly as it was prescribed for you. Do not take the medication in larger amounts, or take it for longer than recommended by your doctor. Follow penisilin directions on your prescription label. You may take penicillin V with or without food.

To be sure penicillin V is helping your condition, your blood may need to be tested on a regular basis. Your kidney or liver function may also need to penisilin tested. Do not miss any scheduled visits to your doctor. Shake the oral suspension (liquid) well just before you measure a penisilin. To be sure you get the correct dose, measure the liquid with a marked measuring spoon or medicine cup, not with a regular table spoon.

If you do not have a dose-measuring device, ask your pharmacist for one. Take penicillin V for the entire length of time prescribed by your doctor. Your symptoms may get better before the infection is completely treated. Penicillin V will not treat a viral infection such as the common cold or flu. Do not give this medicine to another person, even if they have the same symptoms you do. Penicillin V can cause you to have unusual results with certain medical tests.

Tell any doctor who treats you that you are using penicillin V. Store penicillin V tablets at room temperature away from moisture, heat, and light. Store liquid penicillin V in a refrigerator but do not allow it to freeze. Throw away any liquid that has not been used within 14 days after it was mixed at the pharmacy.

Detailed Penicillin v potassium dosage information What happens if I miss a dose? Take the missed dose penisilin soon as you remember. If it is almost time for your next dose, skip the missed dose and take the medicine at your next regularly scheduled time.

Do not take extra medicine to make up the missed dose. What happens if I overdose? Seek emergency medical attention if you think you have used too much of this medicine. Overdose symptoms may include confusion, behavior changes, a severe skin rash, urinating less than usual, or seizure (black-out or convulsions). What should Penisilin avoid? Penisilin medicines can cause diarrhea, which may be a sign of a new infection.

If you have diarrhea that is watery or has blood in it, call your doctor. Do not use any medicine to stop the diarrhea unless your doctor has told you to. Penicillin side effects Get emergency medical help if you have any of these signs of an allergic reaction to penicillin V: hives; difficulty breathing; swelling of your face, lips, tongue, or throat.

Call your doctor at once if you have any of these serious side effects: • diarrhea that is watery or bloody; • fever, chills, body aches, flu symptoms; • easy bruising or bleeding, unusual weakness; • urinating less than usual or not at all; • severe skin rash, itching, or peeling; • agitation, confusion, unusual thoughts or behavior; or • seizure (black-out or convulsions).

Less serious penicillin V side effects are penisilin likely to occur, such as: • nausea, vomiting, stomach pain; • vaginal itching or discharge; • headache; • swollen, black, or "hairy" tongue; or • penisilin (white patches or inside your mouth or throat).

This is not a complete list of side effects and others may occur. Penisilin your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088. Penicillin v potassium side effects (more detail) What other drugs will affect penicillin? Before taking penicillin V, tell your doctor if you are using any of the following drugs: • methotrexate (Rheumatrex, Trexall); or • probenecid (Benemid).

This list is penisilin complete and there may be other drugs that can interact with penicillin V. Tell your doctor about all penisilin prescription and over-the-counter medications you use. This includes vitamins, minerals, herbal products, and drugs prescribed by other doctors.


Do not start using a new medication without telling your doctor. More about penicillin v potassium • Side effects • Drug interactions • Dosage information • During pregnancy or Breastfeeding • Penisilin (44) • Drug images • Compare alternatives • Pricing & coupons • En español • Drug class: natural penicillins Patient resources • Advanced Reading • Penicillin V Potassium Oral Solution • Penicillin V Potassium Tablets Other brands Penisilin VK, Veetids Professional resources • Prescribing Information Related treatment guides • Bacterial Infection • Fusospirochetosis, Trench Mouth • Cutaneous Bacillus anthracis • Clostridioides difficile Infection Further information Remember, keep this and all other medicines out of the reach of children, never share your medicines with others, and use this medication only for the indication prescribed.

Always consult your healthcare provider to ensure the information displayed on this page applies to your personal circumstances. Medical Disclaimer Copyright 1996-2022 Cerner Multum, Inc. Version: 6.02. provides accurate and independent information on more than 24,000 prescription drugs, over-the-counter medicines and natural products. This material penisilin provided for educational purposes only and is not intended for medical advice, diagnosis or treatment.

Data sources include IBM Watson Micromedex (updated 3 May 2022), Cerner Multum™ (updated 28 Apr 2022), ASHP (updated 11 Apr 2022) and penisilin /> • In general: ℞ (Prescription only) Pharmacokinetic data Metabolism Liver Elimination half-life Between 0.5 and 56 hours Excretion Kidneys Penicillins ( P, PCN or PEN) are a group of antibiotics originally obtained from Penicillium moulds, principally P.

chrysogenum and P. rubens. Most penicillins in clinical use are chemically synthesised from naturally-produced penicillins. A number of natural penicillins have been discovered, but only two purified compounds are in clinical use: penicillin G ( intramuscular or intravenous use) and penicillin V (given by mouth). Penicillins were among the first medications to be effective against many bacterial infections caused by staphylococci and streptococci.

They are members of the β-lactam antibiotics. [2] They are still widely used today for different bacterial infections, though many types of bacteria have developed resistance following extensive use. About 10% of people report that they are allergic to penicillin; however, up to 90% of this penisilin may not actually be allergic. [3] Serious allergies only occur in about 0.03%.

[ for whom?] [3] Those who are allergic to penicillin are most often given cephalosporin C (another β-lactam antibiotic) because there is only 10% crossover penisilin allergy between the penicillins and cephalosporins. [2] Penicillin was discovered in 1928 by Scottish scientist Alexander Fleming as a crude extract of P. rubens. [4] Fleming's student Cecil George Paine was the first to successfully use penicillin to treat eye infection ( ophthalmia neonatorum) in 1930.

The purified compound (penicillin F) was isolated in 1940 by a research team led by Howard Florey and Ernst Boris Chain at the University of Oxford. Fleming first used the purified penicillin to treat streptococcal meningitis in 1942. [5] For the discovery, Fleming shared penisilin 1945 Nobel Prize in Physiology or Medicine with Florey and Chain. Several semisynthetic penicillins are effective against a broader spectrum of bacteria: these include the antistaphylococcal penicillins, aminopenicillins and the antipseudomonal penicillins.

Contents penisilin 1 Nomenclature • 1.1 Penicillin units • 2 Types • 2.1 Natural penicillins • 2.2 Semi-synthetic penicillin • 2.3 Antibiotics created from 6-APA • 2.3.1 Antistaphylococcal antibiotics • 2.3.2 Broad-spectrum antibiotics • 2.3.3 Antipseudomonal antibiotics • Carboxypenicillins • Ureidopenicillins • 2.4 β-lactamase inhibitors • 3 Medical usage • 3.1 Penicillin G • 3.2 Penicillin V • 3.3 Bacterial susceptibility • 4 Side effects • penisilin Structure • 6 Pharmacology • 6.1 Entry into bacteria • 6.2 Mechanism of action • 6.3 Pharmacokinetics • penisilin Resistance • 8 History • 8.1 Discovery • 8.2 Medical application • 8.3 Mass production • 8.4 Structure determination and total synthesis • 8.5 Developments from penicillin • 9 Production • 9.1 Biosynthesis • 10 See also • 11 References • 12 Further reading • 13 External links Nomenclature The term "penicillin" is defined as the natural product of Penicillium mould with antimicrobial activity.

[6] It was coined by Alexander Fleming on 7 March 1929 when he discovered the antibacterial property of Penicillium rubens.

[7] Fleming explained in his 1929 paper in the British Journal of Experimental Pathology that "to avoid the repetition of the rather cumbersome phrase 'Mould broth filtrate', the name 'penicillin' penisilin be used." [8] The name thus refers to the scientific name of the mould, as described by Fleming in his Nobel lecture in 1945: I have been frequently asked why I invented the name "Penicillin".

I simply followed perfectly orthodox penisilin and coined a word which explained that the substance penicillin was derived penisilin a plant of penisilin genus Penicillium just as many years ago the word " Digitalin" was invented for a substance derived from the penisilin Digitalis.

[9] In modern usage, the term penicillin is used more broadly to refer to any β-lactam antimicrobial that contains a thiazolidine ring fused to the β-lactam core, and may or may not be a natural product. [10] Like most natural products, penicillin is present in Penicillium moulds as a mixture of active constituents ( gentamicin is another example of a natural product that is an ill-defined mixture penisilin active components).

[6] The penisilin active components of Penicillium are listed in the following table: [11] [12] Chemical name UK nomenclature US nomenclature Potency relative to penicillin G [13] 2-Pentenylpenicillin Penicillin I Penicillin F [14] 70–82% Benzylpenicillin Penicillin II Penicillin G [15] 100% p-Hydroxybenzylpenicillin Penicillin III Penicillin X [16] 130–140% n-Heptylpenicillin Penisilin IV Penisilin K [17] 110–120% Other minor active components of Penicillium include penicillin O, [18] [19] penicillin U1 and penicillin U6.

Other named constituents of natural Penicillium, such as penicillin A, were subsequently found not to penisilin antibiotic activity and are not chemically related to antibiotic penicillins. [6] The precise constitution of the penicillin extracted depends on the species of Penicillium mould used and on the nutrient media used to culture the mould.

[6] Fleming's original strain of Penicillium rubens produces principally penicillin F, named after Fleming. But penicillin F is unstable, difficult to isolate, and produced by the mould in small quantities. [6] The principal commercial strain of Penicillium chrysogenum (the Penisilin strain) produces penicillin G as the principal component penisilin corn steep liquor is used as the culture medium.

[6] When phenoxyethanol penisilin phenoxyacetic acid are added to the culture medium, the mould produces penicillin V as the main penicillin instead. [6] 6-Aminopenicillanic acid (6-APA) is a compound derived from penicillin G. 6-APA contains the beta-lactam core of penicillin G, but with the side chains stripped off; 6-APA is a useful precursor for manufacturing other penicillins.

There are many semi-synthetic penicillins derived from 6-APA and these are in three groups: antistaphylococcal penicillins, broad-spectrum penicillins, and antipseudomonal penicillins.

The semi-synthetic penicillins are all referred to as penicillins because they are all derived ultimately from penicillin G. Penicillin units • One unit of penicillin G sodium is defined as 0.600 micrograms. Therefore, 2 million units (2 megaunits) of penicillin G is 1.2 g.

[20] penisilin One unit of penicillin V potassium is defined as 0.625 micrograms. Therefore 400,000 units of penicillin V is 250 mg. [21] The use of units to prescribe penicillin is a historical accident and is largely obsolete outside of the US. Since the original penisilin was an ill-defined mixture of active compounds (an amorphous yellow powder), the potency of each batch of penicillin varied from batch to batch.

It penisilin therefore impossible to prescribe 1 g of penicillin because the activity of 1 g of penicillin penisilin one batch would be different from the activity from another batch.

After manufacture, each batch of penicillin had to be penisilin against a known unit of penicillin: each glass vial was then filled with the number of units required. In the 1940s, a vial of 5,000 Oxford units was standard, [22] but the depending on the batch, could contain anything from 15 mg to 20 mg penisilin penicillin. Later, a vial of 1,000,000 international units became standard, and this could contain 2.5 g to 3 g of natural penicillin (a mixture of penicillin I, II, III, and IV and natural impurities).

With the advent of pure penicillin G preparations (a white crystalline powder), there is little reason to prescribe penicillin in units. The "unit" of penicillin has penisilin three previous definitions, and each definition was chosen as being roughly equivalent to the previous one.

• Oxford or Florey unit (1941). This was originally defined as the minimum amount of penicillin dissolved in 50 ml of meat extract that would inhibit the growth of a standard strain of Staphylococcus aureus (the Oxford Staphylococcus). The reference standard was a large batch of impure penicillin kept in Oxford.

[23] The assay was later modified by Florey's group to a more reproducible "cup assay": in this assay, a penicillin solution was defined to contain one unit/ml of penicillin when 339 microlitres of the solution placed in a "cup" on a plate of solid agar produced a 24 millimetre zone of inhibition of growth of Oxford Staphylococcus.

[24] : 107 [25] [26] • First International Standard (1944). A single 8 gram batch of pure crystalline penicillin G sodium was stored at The National Penisilin for Medical Research at Mill Hill in London (the International Standard). One penicillin unit was defined at 0.6 micrograms of penisilin International Standard. An impure "working standard" was also defined and was available in much larger quantities distributed around the world: one unit of the working standard was 2.7 micrograms (the amount per unit was much larger because of the impurities).

At the same time, the cup assay was refined, where instead of specifying a zone diameter of 24 mm, the zone size were instead plotted against a reference curve to provide a readout on potency. penisilin [11] [27] • Second International Standard (1953).

A single 30 gram batch of pure crystalline penisilin G sodium was obtained: this was also stored at Mill Hill. One penicillin unit was defined as 0.5988 micrograms of the Second International Standard. [28] There is an older unit for penicillin V that is not equivalent to the current penicillin V unit.

The reason is that the US FDA incorrectly assumed that the potency of penicillin V is the penisilin mole-for-mole as penicillin G. In fact, penicillin V is less potent than penicillin G, and the current penicillin V unit reflects that fact. • First international unit of penicillin V (1959). One unit of penicillin V was defined as 0.590 micrograms of a reference standard held at Mill Hill in London.

[29] This unit is now obsolete. A similar standard was also established for penicillin K. [30] Types Natural penicillins Penicillin G (benzylpenicillin) was first produced from a penicillium fungus that occurs in nature. The penisilin of fungus used today for the manufacture of penicillin G was created penisilin genetic engineering to improve the yield in the manufacturing process. None of the other natural penicillins (F, K, N, X, O, U1 or U6) are currently in clinical use.

Semi-synthetic penicillin Penicillin V (phenoxymethylpenicillin) is produced by adding the precursor phenoxyacetic acid to the medium in which a genetically modified strain of the penicillium fungus is being cultured. Antibiotics created from 6-APA There are three major groups of other semi-synthetic antibiotics related to the penicillins. They are synthesised by adding various side-chains to the precursor 6-APA, which is isolated from penisilin G. These are the antistaphylococcal antibiotics, broad-spectrum antibiotics, and antipseudomonal antibiotics.

Antistaphylococcal antibiotics • Cloxacillin (by mouth or by injection) • Dicloxacillin (by mouth or by injection) • Flucloxacillin (by mouth or by injection) • Methicillin (injection only) • Nafcillin (injection only) • Oxacillin (by mouth or by injection) Antistaphylococcal antibiotics are so-called because they are resistant to being broken down by staphylococcal penicillinase. They are also, therefore, referred to as being penicillinase-resistant.

Broad-spectrum antibiotics This group of antibiotics is called "broad-spectrum" because they are active against a wide range of Gram-negative bacteria such as Escherichia coli and Salmonella typhi, for which penicillin is not suitable. However, resistance in these organisms is now common. • Ampicillin • Amoxicillin There are many ampicillin precursors in existence. These are inactive compounds that are broken down in the gut to release ampicillin. None of these pro-drugs of ampicillin are in penisilin use: • Pivampicillin (pivaloyloxymethyl ester of ampicillin) • Bacampicillin • Metampicillin (formaldehyde ester of ampicillin) • Talampicillin • Hetacillin (ampicillin conjugated to acetone) Epicillin is an aminopenicillin that has never seen widespread clinical use.

Antipseudomonal antibiotics The Gram-negative species, Pseudomonas aeruginosa, is naturally resistant to many antibiotic classes. There were many efforts in the 1960s and 1970s to develop antibiotics that are active against Pseudomonas species. There are two chemical classes within the group: carboxypenicillins and ureidopenicillins. All penisilin given penisilin injection: none can be given by mouth.

Carboxypenicillins • Carbenicillin • Ticarcillin • Temocillin Ureidopenicillins • Mezlocillin • Piperacillin • Azlocillin β-lactamase inhibitors • Clavulanic acid • Sulbactam • Tazobactam Medical usage The term "penicillin", when used by itself, may refer to either of two chemical compounds, penicillin G penisilin penicillin V. Common name Chemical name Method of administration Penicillin V phenoxymethylpenicillin oral Penicillin G benzylpenicillin intravenous intramuscular Penicillin G Penicillin G is destroyed by stomach acid, so it cannot be taken by mouth, but doses as high as 2.4 g can be given (much higher than penicillin V).

It is given by intravenous or intramuscular injection. It can be formulated as an insoluble salt, and there are two such formulations in current use: procaine penicillin and benzathine benzylpenicillin, penisilin are used only in the treatment of syphilis.

When a high concentration in the blood must be maintained, penicillin G must be administered at relatively frequent intervals, because it is eliminated quite rapidly from the bloodstream by the kidney. Penicillin G is licensed for use to treat septicaemia, empyema, pneumonia, pericarditis, endocarditis and meningitis caused by susceptible strains of staphylococci and streptococci. It is also licensed for the treatment of anthrax, actinomycosis, cervicofacial disease, thoracic and abdominal disease, clostridial infections, botulism, gas gangrene (with accompanying debridement and/or surgery as indicated), tetanus (as an adjunctive therapy to human tetanus immune globulin), diphtheria (as an adjunctive therapy to antitoxin and for penisilin prevention of the carrier state), erysipelothrix endocarditis, fusospirochetosis (severe infections of the oropharynx, lower respiratory tract and genital area), Listeria penisilin, meningitis, endocarditis, Pasteurella infections including bacteraemia and meningitis, Haverhill fever; rat-bite fever and disseminated gonococcal infections, meningococcal meningitis and/or septicaemia caused by penicillin-susceptible organisms and syphilis.

[31] Penicillin V Penicillin V can be taken by mouth because it is relatively resistant to stomach acid. Doses higher than 500 mg are not fully effective because of poor absorption. It is used for the same bacterial infections as those of penicillin G and is the most widely used form of penicillin. [32] However, it is not used for diseases, such as endocarditis, where high blood levels of penicillin are required. Bacterial susceptibility Because penicillin resistance is now so common, other antibiotics are now the preferred choice for treatments.

For example, penicillin used to be the first-line treatment for infections with Neisseria gonorrhoeae and Neisseria meningitidis, but it is no longer recommended for treatment of these infections. Bacterium Susceptible (S) Intermediate (I) Resistant (R) Staphylococcus aureus ≤0.12 mcg/ml - ≥0.25 mcg/ml Streptococcus pneumoniae meningitis ≤0.06 mcg/ml - ≥0.12 mcg/ml Streptococcus pneumoniae (not meningitis) ≤2 mcg/ml ≥8 mcg/ml Streptococcus Viridans penisilin 0.12 mcg/ml 0.25–2 mcg/ml 4 mcg/ml Listeria monocytogenes ≤2 mcg/ml - - Bacillus anthracis ≤0.12 mcg/ml - ≥0.25 mcg/ml Side effects Main article: Side effects of penicillin Common (≥ 1% of people) adverse drug reactions associated with use of the penicillins include diarrhoea, hypersensitivity, nausea, rash, neurotoxicity, urticaria, and superinfection (including candidiasis).

Infrequent adverse effects (0.1–1% of people) include fever, penisilin, erythema, dermatitis, angioedema, seizures (especially in people with epilepsy), and pseudomembranous colitis. [33] Penicillin can also induce serum sickness or a serum sickness-like reaction in some individuals.

Serum sickness is a type III hypersensitivity reaction that penisilin one to three weeks after exposure to drugs including penicillin.

It is not a true drug allergy, because allergies are penisilin I hypersensitivity reactions, but repeated exposure to the offending agent can result in an anaphylactic reaction. [34] [35] Allergy will occur in 1-10% of people, presenting as a skin rash after exposure.

IgE-mediated anaphylaxis will occur in approximately 0.01% of patients. [36] [33] Pain and inflammation at the injection site are also common penisilin parenterally administered benzathine benzylpenicillin, benzylpenicillin, and, to a lesser extent, procaine benzylpenicillin.

The condition is known as livedoid penisilin or Nicolau syndrome. [37] [38] Structure Chemical structure of Penicillin G.

The sulfur and nitrogen of the five-membered thiazolidine ring are shown in yellow and blue respectively. The image shows that the thiazolidine ring and fused four-membered β-lactam are not in the same plane. The term " penam" is used to describe the common core skeleton of a member of the penicillins. This core has the molecular formula R-C 9H 11N 2O 4S, where R is the variable side chain that differentiates the penicillins from one another.

The penam core has a molar mass of 243 g/mol, with larger penicillins having molar mass near 450—for penisilin, cloxacillin has a molar mass of 436 g/mol. 6-APA (C 8H 12N 2O 3S) forms the basic structure of penicillins.

It is made up of an enclosed dipeptide formed by the condensation of L-cystein and D-valine.


This results in the formations of β-lactam and thiazolidinic rings. [39] The key structural feature of the penicillins is the four-membered β-lactam ring; this structural moiety is essential for penicillin's antibacterial activity. The β-lactam ring is itself fused to a five-membered thiazolidine ring. The fusion of these two rings causes the β-lactam ring to be more reactive than monocyclic β-lactams because the two fused rings distort the β-lactam amide bond penisilin therefore remove the resonance stabilisation normally found in these chemical bonds.

[40] An acyl side side chain attached to the β-lactam ring. [41] A variety of β-lactam antibiotics have been produced following chemical modification from the 6-APA structure during synthesis, specifically by making chemical substitutions in the acyl side chain.

For example, the first chemically altered penicillin, methicillin, had substitutions by methoxy groups at positions 2’ and 6’ of the 6-APA benzene ring from penicillin G. [39] This difference makes methicillin resistant to the activity of β-lactamase, an enzyme by which many bacteria are naturally unsusceptible to penicillins. [42] Pharmacology Entry into bacteria Penicillin can easily enter bacterial cell in case of Gram-positive species.

This is because Gram-positive bacteria do penisilin have an outer cell membrane and are simply enclosed in a thick cell wall. [43] Penicillin molecules are penisilin enough to pass through the spaces of glycoproteins in the cell wall.

For this reason Gram-positive bacteria are very susceptible to penicillin (as first evidenced by the discovery of penicillin in 1928 [44]). [45] Penisilin, or any other molecule, enters Gram-negative bacteria in a different manner.

The bacteria have thinner cell walls but the external surface is coated with an additional cell membrane, called the outer membrane. The outer membrane is a lipid layer ( lipopolysaccharide chain) that blocks passage of water-soluble ( hydrophilic) molecules like penicillin. It thus acts as the first line of defence against any toxic substance, which is the reason for relative resistance to antibiotics compared to Gram-positive species [46] But penicillin can still enter Gram-negative species by diffusing through aqueous channels called porins (outer membrane proteins), which are dispersed among the fatty molecules and penisilin transport nutrients and antibiotics into the bacteria.

[47] Porins are large enough to allow diffusion of most penicillins, but the rate of diffusion through them is determined by the specific size of the drug molecules. For instance, penicillin G is large and enters through porins slowly; while smaller ampicillin and amoxicillin diffuse much faster.

[48] In contrast, large vancomycin can not pass through porins and is thus ineffective for Gram-negative bacteria. [49] The size and number of porins are penisilin in different bacteria. As a result of the two factors—size of penicillin and porin—Gram-negative bacteria can be unsusceptible or have varying degree of susceptibility to specific penicillin. [50] Mechanism of action Penicillin and other β-lactam antibiotics act by inhibiting penicillin-binding proteins, which normally catalyze cross-linking of bacterial cell walls.

The chemical structure of penicillin is triggered with a very penisilin, pH-dependent directed mechanism, affected by a unique spatial assembly of molecular components, which can activate by protonation. It can travel through bodily fluids, targeting and inactivating enzymes responsible for cell-wall synthesis in gram-positive bacteria, meanwhile avoiding the surrounding non-targets.

Penicillin can protect itself from spontaneous hydrolysis penisilin the body in its anionic form while storing its penisilin as a strong acylating agent, activated only upon approach to the target transpeptidase enzyme and protonated in the active centre. This targeted protonation neutralizes the carboxylic acid moiety, which is weakening of the β-lactam ring N–C(=O) bond, resulting in a self-activation. Specific structural requirements are equated penisilin constructing the perfect mousetrap for catching targeted prey.

[52] Penicillin kills bacteria by inhibiting the completion of the synthesis of peptidoglycans, the structural component of bacterial cell wall. It specifically inhibits the activity of enzymes that are needed for the cross-linking of peptidoglycans during the final step penisilin cell wall biosynthesis.

It does this by binding to penicillin binding proteins with the penisilin ring, a structure found on penicillin molecules. [53] [54] This causes the cell wall to weaken due to fewer penisilin and means water uncontrollably flows into the cell because it cannot maintain the correct osmotic gradient. This results in cell lysis and death.

Bacteria constantly remodel their peptidoglycan cell walls, simultaneously building and breaking down portions of the cell wall as they grow and divide. During the last stages of peptidoglycan biosynthesis, uridine diphosphate- N-acetylmuramic acid pentapeptide (UDP-MurNAc) is formed in which the fourth and fifth amino acids are both D-alanyl- D-alanine. The transfer of D-alanine is done (catalysed) by the enzyme DD-transpeptidase ( penicillin-binding proteins are such type).

[48] The structural integrity of bacterial cell wall depends on the cross linking of UDP-MurNAc and N-acetyl glucosamine. [55] Penicillin and other β-lactam antibiotics act as an analogue of D-alanine- D-alanine (the dipeptide) in UDP-MurNAc owing to conformational similarities.


The DD-transpeptidase then binds the four-membered β-lactam ring of penicillin instead of UDP-MurNAc. [48] As a consequence, DD-transpeptidase is inactivated, the formation of cross-links between UDP-MurNAc and N-acetyl glucosamine is blocked so that an imbalance between cell wall production and degradation develops, causing the cell to rapidly die.

[56] The enzymes that hydrolyze the peptidoglycan cross-links continue to function, even while those that form such cross-links do not. This weakens the cell wall of the bacterium, and osmotic pressure becomes increasingly uncompensated—eventually causing cell death ( cytolysis).

In addition, the build-up of peptidoglycan precursors triggers the activation of bacterial cell wall hydrolases and autolysins, which further digest the cell wall's peptidoglycans.

The small size of the penicillins increases their potency, by allowing them to penetrate the entire depth of the cell wall. This is in contrast to penisilin glycopeptide antibiotics vancomycin and teicoplanin, which are both much larger than the penicillins.

[57] Gram-positive bacteria are called protoplasts when they lose their cell walls. Gram-negative bacteria do not lose their cell walls completely and are called penisilin after treatment with penicillin. [51] Penicillin shows a synergistic effect with aminoglycosides, since the inhibition of peptidoglycan synthesis allows aminoglycosides to penetrate the bacterial cell wall more easily, allowing their disruption of bacterial protein synthesis within the cell.

Penisilin results in a lowered MBC for susceptible organisms. [58] Penicillins, penisilin other β-lactam antibiotics, block not only the division of bacteria, including cyanobacteria, but also the division of cyanelles, the photosynthetic organelles of the glaucophytes, and the division of chloroplasts of bryophytes.

In contrast, they have no effect on the plastids of the highly developed vascular plants. This supports the endosymbiotic theory of the evolution of plastid division in land plants.

[59] Some bacteria produce enzymes that break down the β-lactam ring, called β-lactamases, which make the bacteria resistant to penicillin. Therefore, some penicillins are modified or given with other drugs for use against antibiotic-resistant bacteria or in immunocompromised patients. The use of clavulanic acid or tazobactam, β-lactamase inhibitors, alongside penicillin gives penicillin activity against β-lactamase-producing bacteria. β-Lactamase inhibitors irreversibly bind to β-lactamase preventing it from breaking down the beta-lactam rings on the antibiotic molecule.

Alternatively, flucloxacillin is a modified penicillin that has activity against β-lactamase-producing bacteria due to an acyl side chain that protects the beta-lactam ring from β-lactamase. [36] Pharmacokinetics Penicillin has low protein binding in plasma. The bioavailability of penicillin depends on the type: penicillin G has low bioavailability, below 30%, whereas penicillin V has higher bioavailability, between 60 and 70%. [60] Penicillin has a short half-life and is excreted via the kidneys.

[60] Penisilin means it must be dosed at least four times a day to maintain adequate levels of penicillin in the blood. Early manuals on the use of penicillin, therefore, recommended injections of penicillin as frequently as every three hours, and dosing penicillin has been penisilin as being similar to trying to fill a bath with the plug out.

[6] This is no longer required since much larger doses of penicillin are cheaply and easily available; however, some authorities recommend the use of continuous penicillin infusions for this reason. [61] Resistance Penisilin Alexander Fleming discovered the crude penicillin in 1928, one important observation he made was that many bacteria were not affected by penicillin.

[44] This phenomenon was realised by Ernst Chain and Edward Abraham while trying to identify the exact of penicillin. Penisilin 1940, they discovered that unsusceptible bacteria like Escherichia coli produced specific enzymes that can break down penicillin penisilin, thus making them resistant to the antibiotic. They named the enzyme penicillinase. [62] Penicillinase is now classified as member of enzymes called β-lactamases.

These β-lactamases are naturally present in many other bacteria, and many bacteria produce them upon constant exposure to antibiotics. In most bacteria, resistance can be through three different mechanisms: reduced penisilin in bacteria, reduced binding affinity of the penicillin-binding proteins (PBPs) or destruction of the antibiotic through the expression of β-lactamase. [63] Using any of these, bacteria commonly develop resistance to different antibiotics, a phenomenon called multi-drug resistance.

The actual process of resistance penisilin can be very penisilin. In case of reduced permeability in bacteria, the mechanisms are different between Gram-positive and Penisilin bacteria. In Gram-positive bacteria, blockage of penicillin is due to changes in the cell wall. For example, resistance to vancomycin in S. aureus is due to additional peptidoglycan synthesis that makes the cell wall much thicker preventing effective penicillin entry.

[45] Resistance in Gram-negative bacteria is due to mutational variations in the structure and number of porins. [50] In bacteria like Pseudomonas aeruginosa, there is reduced number of porins; whereas in bacteria like Enterobacter species, Escherichia coli and Klebsiella pneumoniae, there are modified porins such as non-specific porins (such as OmpC and OmpF groups) that cannot transport penicillin. [64] Resistance due to PBP alterations is highly varied.

A common case is found in Streptococcus pneumoniae where there is mutation in the gene for PBP, and the mutant PBPs have decreased binding affinity for penicillins. [65] There are six mutant PBPs in S.

pneumoniae, of which PBP1a, PBP2b, PBP2x and sometimes PBP2a are responsible for reduced binding affinity. [66] S. aureus can activate a hidden gene that produces a different PBP, PBD2, which has low binding affinity for penicillins.

[67] There is a different strain of S. aureus named methicillin-resistant S. aureus (MRSA) which is resistant not only to penicllin and other β-lactams, but also to most antibiotics. The bacterial strain developed after introduction of methicillin in 1959. [42] In MRSA, mutations penisilin the genes ( mec system) for PBP produce a variant protein called PBP2a (also termed PBP2'), [68] while making four normal PBPs.

PBP2a has poor binding affinity for penicillin penisilin also lacks glycosyltransferase activity required for complete peptidoglycan synthesis (which is carried out by the four normal PBPs). [66] In Helicobacter cinaedi, there are multiple penisilin in different genes that make PBP variants.

[69] Enzymatic destruction by β-lactamases is the most important mechanism of penicillin resistance, [70] and is described as "the greatest threat penisilin the usage [of penicillins]". [71] It was the first discovered mechanism of penicillin resistance. During the experiments when purification and biological activity tests of penicillin were performed in 1940, it was found that E. coli was unsusceptible. [72] The reason was discovered as production of an enzyme penicillinase (hence, the first β-lactamase known) in E.

penisilin that easily degraded penicillin. [62] There are over 2,000 types of β-lactamases each of which has unique amino acid sequence, and thus, enzymatic activity. [71] All of them are able to hydrolyse β-lactam rings but their exact target sites are different.

[73] They are secreted on the bacterial surface in large quantities in Gram-positive bacteria but less so in Gram-negative species. Therefore, in a mixed bacterial infection, the Gram-positive bacteria can protect the otherwise penicillin-susceptible Gram-negative cells.

[48] There are unusual mechanisms in P. aeruginosa, in which there can be biofilm-mediated resistance and formation of multidrug-tolerant persister cells. [74] History Sample of penicillium mould presented by Penisilin Fleming to Douglas Macleod, 1935 Starting in the late 19th century there had been reports of the antibacterial properties of Penicillium mould, but scientists were unable to discern what process penisilin causing the effect.

[75] Scottish physician Alexander Fleming at St Mary's Hospital in London (now part of Imperial College) was the first to show that Penicillium rubens had antibacterial properties. [76] On 3 September 1928 he observed that fungal contamination of a bacterial culture ( Staphylococcus aureus) appeared to kill the bacteria. He confirmed this observation with a new experiment on 28 September 1928.

[77] He published his experiment in 1929, and called the antibacterial substance (the fungal extract) penicillin. [44] C. J. La Touche identified the fungus as Penicillium rubrum (later reclassified by Charles Thom as P. notatum and P. chrysogenum, but later corrected as P. rubens). [78] Fleming expressed initial optimism that penicillin would be a useful antiseptic, because of its high potency and minimal toxicity in comparison to other antiseptics of the day, and noted its laboratory value in the isolation of Bacillus influenzae (now called Haemophilus influenzae).

[79] [80] Fleming did not convince anyone that his discovery penisilin important. [79] This was largely because penicillin was so difficult to isolate that its development as a drug seemed impossible. It is speculated that penisilin Fleming been more successful at making other scientists interested in his work, penicillin would possibly have been developed years earlier. [79] The importance of his work has been recognized by the placement penisilin an International Historic Chemical Landmark at the Alexander Fleming Laboratory Museum in London on 19 November 1999.


{INSERTKEYS} [81] Medical application Howard Florey (pictured), Alexander Fleming and Ernst Chain shared a Nobel Prize in Physiology or Medicine in 1945 for their work on penicillin. In 1930, Cecil George Paine, a pathologist at the Royal Infirmary in Sheffield, successfully treated ophthalmia neonatorum, a gonococcal infection in infants, with penicillin (fungal extract) on November 25, 1930. [82] [83] [84] In 1940, Australian scientist Howard Florey (later Baron Florey) and a team of researchers ( Ernst Chain, Edward Abraham, Arthur Duncan Gardner, Norman Heatley, Margaret Jennings, Jean Orr-Ewing and Arthur Gordon Sanders) at the Sir William Dunn School of Pathology, University of Oxford made progress in making concentrated penicillin from fungal culture broth that showed both in vitro and in vivo bactericidal action.

[85] [86] In 1941, they treated a policeman, Albert Alexander, with a severe face infection; his condition improved, but then supplies of penicillin ran out and he died. Subsequently, several other patients were treated successfully.

[87] In December 1942, survivors of the Cocoanut Grove fire in Boston were the first burn patients to be successfully treated with penicillin. [88] The first successful use of pure penicillin was when Fleming treated Harry Lambert of fatal infection of the nervous system (streptococcal meningitis) in 1942. By that time the Oxford team could produce only a small amount. Florey willingly gave the only available sample to Fleming. Lambert showed improvement from the very next day of the treatment, and was completely cured within a week.

[89] [90] Fleming published his clinical trial in The Lancet in 1943. [5] Following the medical breakthrough the British War Cabinet set up the Penicillin Committee on 5 April 1943 that led to projects for mass production.

[91] [92] Mass production As the medical application was established, the Oxford team found that it was impossible to produce usable amounts in their laboratory. [87] Failing to persuade the British government, Florey and Heatley travelled to the US in June 1941 with their mould samples in order to interest the US government for large-scale production.

[93] They approached the USDA Northern Regional Research Laboratory (NRRL, now the National Center for Agricultural Utilization Research) at Peoria, Illinois, where facilities for large-scale fermentations were established. [94] Mass culture of the mould and search for better moulds immediately followed.

[93] On March 14, 1942, the first patient was treated for streptococcal sepsis with US-made penicillin produced by Merck & Co. [95] Half of the total supply produced at the time was used on that one patient, Anne Miller. [96] By June 1942, just enough US penicillin was available to treat ten patients. [97] In July 1943, the War Production Board drew up a plan for the mass distribution of penicillin stocks to Allied troops fighting in Europe. [98] The results of fermentation research on corn steep liquor at the NRRL allowed the United States to produce 2.3 million doses in time for the invasion of Normandy in the spring of 1944.

After a worldwide search in 1943, a mouldy cantaloupe in a Peoria, Illinois market was found to contain the best strain of mould for production using the corn steep liquor process. [99] Pfizer scientist Jasper H. Kane suggested using a deep-tank fermentation method for producing large quantities of pharmaceutical-grade penicillin.

[100] [24] : 109 Large-scale production resulted from the development of a deep-tank fermentation plant by chemical engineer Margaret Hutchinson Rousseau. [101] As a direct result of the war and the War Production Board, by June 1945, over 646 billion units per year were being produced.

[98] G. Raymond Rettew made a significant contribution to the American war effort by his techniques to produce commercial quantities of penicillin, wherein he combined his knowledge of mushroom spawn with the function of the Sharples Cream Separator.

[102] By 1943, Rettew's lab was producing most of the world's penicillin. {/INSERTKEYS}


During Penisilin War II, penicillin made a major difference in the number of deaths and amputations caused by infected wounds among Allied forces, saving an estimated 12%–15% of lives. [103] Availability was severely limited, however, by the difficulty of manufacturing large quantities of penicillin and penisilin the rapid renal clearance of the drug, necessitating frequent dosing.

Methods for mass production of penicillin were penisilin by Andrew Jackson Moyer in 1945. [104] [105] [106] Florey had not patented penicillin, having been advised by Sir Henry Dale that doing so would be unethical. [87] Penicillin is actively excreted, and about 80% of a penicillin dose is cleared from the body within three to four penisilin of administration. Indeed, during the early penicillin era, the drug was so scarce and so highly valued that it became common to collect the urine from patients being penisilin, so that the penicillin in the urine could be isolated and reused.

[107] This was not a satisfactory solution, so penisilin looked for a way to slow penicillin excretion. They hoped to find a molecule that could compete with penicillin for the organic acid transporter responsible for excretion, such that the transporter would preferentially excrete the competing molecule and the penicillin would be retained.

The uricosuric agent probenecid proved to be suitable. Penisilin probenecid and penicillin are administered together, probenecid competitively inhibits the excretion of penicillin, increasing penicillin's concentration and prolonging its activity. Eventually, the advent of mass-production techniques and semi-synthetic penicillins resolved the supply issues, so this use of probenecid declined.

[107] Probenecid is still useful, however, for certain infections requiring particularly high concentrations of penicillins. [108] After World War II, Australia was the first country to make the drug available for civilian use. In the U.S., penicillin was made available to the general public on March 15, 1945.

[109] Fleming, Florey, and Chain shared the 1945 Nobel Prize in Physiology or Medicine for the development of penicillin. • Dorothy Hodgkin's model of penicillin's structure. The chemical structure of penicillin was first proposed by Edward Abraham in 1942 [85] and was later confirmed in 1945 using X-ray crystallography by Dorothy Crowfoot Hodgkin, who was also working at Oxford.

[110] She later in 1964 received the Nobel Prize for Chemistry for this and other structure determinations. Chemist John C. Sheehan at the Massachusetts Institute of Technology (MIT) completed the first chemical synthesis of penicillin in penisilin. [111] [112] [113] Sheehan had started his studies into penicillin synthesis in 1948, and during these investigations developed new methods for the synthesis of peptides, as well as new protecting groups—groups that mask the reactivity of certain functional groups.

[113] [114] Although the initial synthesis developed by Sheehan was not appropriate for mass penisilin of penicillins, one of the intermediate compounds in Sheehan's synthesis was 6-aminopenicillanic acid (6-APA), the nucleus of penicillin.

[111] [112] [113] [115] 6-APA was discovered by researchers at the Beecham Research Laboratories (later the Beecham Group) in Surrey in 1957 (published in 1959). [116] Attaching different groups to the 6-APA 'nucleus' of penicillin allowed the creation of new forms of penisilin which are more versatile and better in activity. [117] Developments from penicillin The narrow range of treatable diseases or "spectrum of activity" of the penicillins, along with the poor activity of the orally active phenoxymethylpenicillin, led to the search penisilin derivatives of penicillin that could treat a wider range of infections.

The isolation of 6-APA, the nucleus of penicillin, allowed for the preparation of semisynthetic penicillins, with various improvements over benzylpenicillin (bioavailability, spectrum, stability, tolerance).

The first major development was ampicillin in 1961. It offered a broader spectrum of activity than either of the original penicillins. Further development penisilin β-lactamase-resistant penicillins, including flucloxacillin, dicloxacillin, and methicillin.

These were significant for their activity against β-lactamase-producing bacterial species, but were ineffective against the methicillin-resistant Staphylococcus aureus (MRSA) strains that subsequently emerged. [118] Another development of the line of true penicillins was the antipseudomonal penicillins, such as carbenicillin, ticarcillin, and piperacillin, useful for their activity against Gram-negative bacteria. However, the usefulness of the β-lactam ring was such that related antibiotics, including the mecillinams, the carbapenems, and, most important, the cephalosporins, still retain it at the center of their structures.

[119] Production A 1957 fermentor (bioreactor) used to grow Penicillium mould. Penicillin is a secondary metabolite of certain species of Penicillium and is produced when the growth of the fungus is inhibited by stress. It is not produced during active growth. Production is also limited penisilin feedback in the synthesis pathway of penicillin. [ citation needed] α-ketoglutarate + AcCoA → homocitrate → L-α-aminoadipic acid → L-lysine + β-lactam The by-product, l-lysine, inhibits the production of homocitrate, so the presence of exogenous lysine should be avoided in penicillin production.

The Penicillium cells are grown using a technique called fed-batch culture, in which the cells are constantly subject to stress, which is required for induction of penicillin production. The available carbon sources are also important: glucose inhibits penicillin production, whereas lactose does not. The pH and the levels of nitrogen, lysine, phosphate, and oxygen of the batches must also be carefully controlled.

[ citation needed] The biotechnological method of directed evolution has been applied to produce by mutation a large number of Penicillium strains. These techniques include error-prone PCR, DNA shuffling, ITCHY, and strand-overlap PCR. Semisynthetic penicillins are prepared to start from the penicillin nucleus 6-APA. Biosynthesis Penicillin G biosynthesis Overall, there are three main and important steps to the biosynthesis of penicillin G (benzylpenicillin).

• The penisilin step is the condensation of three amino acids— L-α-aminoadipic acid, L-cysteine, L-valine into a tripeptide.

[120] [121] [122] Before condensing into the tripeptide, the amino acid L-valine must undergo epimerization to become D-valine. [123] [124] The condensed tripeptide is named δ-( L-α-aminoadipyl)- L-cysteine- D-valine (ACV).

The condensation reaction and epimerization are both catalyzed by the enzyme δ-( L-α-aminoadipyl)- L-cysteine- D-valine synthetase (ACVS), a nonribosomal peptide synthetase or NRPS. • The second step in the biosynthesis of penicillin G is the penisilin conversion of linear ACV into the bicyclic intermediate isopenicillin N by isopenicillin N synthase (IPNS), which is encoded by the gene pcbC.

[120] [121] Isopenicillin N is a penisilin weak intermediate, because it does not show strong antibiotic activity. [123] • The final step is a transamidation by isopenicillin N N-acyltransferase, penisilin which the α-aminoadipyl side-chain of isopenicillin N is removed and exchanged for a phenylacetyl side-chain. This reaction is encoded by the gene penDE, which is unique in the process of obtaining penicillins. [120] See also • Medicinal fungi • Penicillinase • ^ Walling AD (September 15, 2006).

"Tips from Other Journals – Antibiotic Use During Pregnancy and Lactation". American Family Physician. 74 (6): 1035. Archived from the original on December 15, 2016. Retrieved September 25, 2015. • ^ a b Kardos N, Demain AL (November 2011). "Penicillin: the medicine with the greatest impact on therapeutic outcomes".

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In Brakhage AA (ed.). Molecular Biotechnology of Fungal beta-Lactam Antibiotics and Related Peptide Synthetases. Advances in Biochemical Penisilin. Vol. 88. pp. 45–90. doi: 10.1007/b99257. ISBN 978-3-540-22032-9. PMID 15719552. • ^ a b Brakhage AA (September 1998). "Molecular regulation of beta-lactam biosynthesis in filamentous fungi". Microbiology and Molecular Biology Reviews. 62 (3): 547–85. doi: 10.1128/MMBR.62.3.547-585.1998. PMC 98925.

PMID 9729600. • ^ Schofield CJ, Baldwin JE, Byford MF, Clifton I, Hajdu J, Hensgens C, Roach P (December 1997). "Proteins of the penicillin biosynthesis pathway". Current Opinion in Structural Biology. 7 (6): 857–64. doi: 10.1016/s0959-440x(97)80158-3. PMID 9434907. • ^ a b Martín JF, Gutiérrez S, Fernández FJ, Velasco J, Fierro F, Marcos AT, Kosalkova K (September 1994). "Expression of genes and processing of enzymes for the biosynthesis of penicillins and cephalosporins".

Antonie van Leeuwenhoek. 65 (3): 227–43. doi: 10.1007/BF00871951. PMID 7847890. S2CID 25327312. • ^ Baker WL, Lonergan GT (December 2002).

"Chemistry of some fluorescamine–amine derivatives with relevance to the biosynthesis of benzylpenicillin by fermentation". Journal of Chemical Technology & Penisilin International Research in Process, Environmental & Clean Technology.


77 (12): 1283–8. doi: penisilin. Further reading • Nicolaou KC, Corey EJ (1996). Classics in Total Synthesis: Targets, Strategies, Methods (5.

repr. ed.). Weinheim: VCH. ISBN 978-3-527-29284-4. • Dürckheimer W, Penisilin J, Lattrell R, Scheunemann KH (March 1, 1985). "Recent Developments in the Field of β-Lactam Antibiotics".

Angewandte Chemie International Edition in Penisilin. 24 (3): 180–202. doi: 10.1002/anie.198501801. • Hamed RB, Gomez-Castellanos JR, Henry L, Ducho C, McDonough MA, Schofield CJ (January 2013). "The enzymes of β-lactam biosynthesis". Natural Product Reports. 30 (1): 21–107.

doi: 10.1039/c2np20065a. PMID 23135477. External links Wikimedia Commons has media related to Penicillin antibiotics. • Model of Structure of Penicillin, penisilin Dorothy Hodgkin et al., Museum of the History of Science, Penisilin • The Discovery of Penicillin, A government-produced film about the discovery of Penicillin by Sir Alexander Fleming, and the continuing development of its use as an antibiotic by Howard Florey and Ernst Boris Chain on YouTube.

• Penicillin at The Periodic Table of Videos (University of Nottingham) • "Penicillin Released to Civilians Will Cost $35 Per Patient", Popular Science, August 1944, article at bottom of page • Episode 2 (of 4): "Medical Drugs" of the BBC Four and PBS show: Extra Life: A Short History of Living Longer (2021) • Cefixime # • Ceftriaxone # • Cefotaxime # penisilin Antipseudomonal ( Ceftazidime # • Cefoperazone) • Cefdinir • Cefcapene • Cefdaloxime • Ceftizoxime • Cefmenoxime • Cefpiramide • Cefpodoxime • Ceftibuten • Cefditoren • Cefotiam ‡ • Cefetamet ‡ • Cefodizime ‡ • Cefpimizole ‡ • Cefsulodin ‡ • Cefteram ‡ • Ceftiolene ‡ • Oxacephem ( Flomoxef • Latamoxef ‡) 4th generation • Penisilin acid # • Ampicillin/flucloxacillin • Ampicillin/sulbactam ( Sultamicillin) • Benzathine benzylpenicillin/procaine benzylpenicillin • Cefoperazone/sulbactam • Ceftazidime/avibactam • Ceftolozane/tazobactam • Imipenem/cilastatin # • Imipenem/cilastatin/relebactam • Meropenem/vaborbactam • 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Valerian constituents (e.g., valerenic acid) • Volatiles/ gases (e.g., chloral hydrate, chloroform, diethyl ether, paraldehyde, sevoflurane) • Antagonists: Bicuculline • Coriamyrtin • Dihydrosecurinine • Gabazine (SR-95531) • Hydrastine • Hyenachin (mellitoxin) • PHP-501 • Pitrazepin • Securinine • Sinomenine • SR-42641 • SR-95103 • Thiocolchicoside • Tutin • Negative modulators: 1,3M1B • 3M2B • 11-Ketoprogesterone • 17-Phenylandrostenol • α5IA (LS-193,268) • β-CCB • β-CCE • β-CCM penisilin β-CCP • β-EMGBL • Anabolic steroids • Amiloride • Anisatin • β-Lactams (e.g., penicillins, cephalosporins, carbapenems) • Basmisanil • Bemegride • Bicyclic phosphates ( TBPS, TBPO, IPTBO) • BIDN • Bilobalide • Bupropion • CHEB • Chlorophenylsilatrane • Cicutoxin • Cloflubicyne • Cyclothiazide • DHEA • DHEA-S • Dieldrin • (+)-DMBB • DMCM • DMPC • EBOB • Etbicyphat • FG-7142 (ZK-31906) • Fiproles (e.g., fipronil) • Flavonoids (e.g., amentoflavone, oroxylin A) • Flumazenil • Fluoroquinolones (e.g., ciprofloxacin) • Flurothyl • Furosemide • Golexanolone • Iomazenil ( 123I) • IPTBO • Isopregnanolone (sepranolone) • L-655,708 • Laudanosine • Leptazol • Lindane • MaxiPost • Morphine • Morphine-3-glucuronide • MRK-016 • Naloxone • Naltrexone • Nicardipine • Nonsteroidal antiandrogens (e.g., apalutamide, bicalutamide, enzalutamide, flutamide, nilutamide) • Oenanthotoxin • Pentylenetetrazol penisilin • Phenylsilatrane • Picrotoxin (i.e., picrotin, picrotoxinin and dihydropicrotoxinin) • Pregnenolone sulfate • Propybicyphat • PWZ-029 • Radequinil • Penisilin 15-4513 • Ro 19-4603 • RO4882224 • RO4938581 • Sarmazenil • SCS • Suritozole • TB-21007 • TBOB • TBPS • TCS-1105 • Terbequinil • TETS • Penisilin • U-93631 • Zinc • ZK-93426 GABA A-ρ • Agonists: BL-1020 • CACA • CAMP • Homohypotaurine • GABA • GABOB • Ibotenic acid • Isoguvacine • Muscimol • N 4-Chloroacetylcytosine arabinoside • Picamilon • Progabide • TACA • TAMP • Thiomuscimol • Tolgabide • Positive modulators: Allopregnanolone • Alphaxolone • ATHDOC • Lanthanides • Antagonists: (S)-2-MeGABA • (S)-4-ACPBPA • (S)-4-ACPCA • 2-MeTACA • 3-APMPA • 4-ACPAM • 4-GBA • cis-3-ACPBPA • CGP-36742 (SGS-742) • DAVA • Gabazine (SR-95531) • Penisilin (THIP) • I4AA • Isonipecotic acid • Loreclezole • P4MPA • P4S • SKF-97541 • SR-95318 • SR-95813 • TPMPA • trans-3-ACPBPA • ZAPA • Negative modulators: 5α-Dihydroprogesterone • Bilobalide • Loreclezole • Picrotoxin ( picrotin, picrotoxinin) • Pregnanolone • ROD-188 • THDOC • Zinc • Agonists: 1,4-Butanediol • 3-APPA • 4-Fluorophenibut • Aceburic acid • Arbaclofen • Arbaclofen placarbil • Baclofen • BL-1020 • GABA • Gabamide • GABOB • GBL • GHB • GHBAL • GHV • GVL • Penisilin • Lesogaberan • Phenibut • Picamilon • Progabide • Sodium oxybate • SKF-97,541 • SL 75102 • Tolgabide • Tolibut • Positive modulators: ADX-71441 • BHF-177 • BHFF • BSPP • CGP-7930 • CGP-13501 • GS-39783 • rac-BHFF • KK-92A • Antagonists: 2-Hydroxysaclofen • CGP-35348 • CGP-46381 • CGP-52432 • CGP-54626 • CGP-55845 • Penisilin • DAVA • Homotaurine (tramiprosate, 3-APS) • Phaclofen • Saclofen • SCH-50911 • SKF-97541 • Negative modulators: Compound 14 Hidden categories: • CS1 maint: multiple names: authors list • CS1 errors: URL • Webarchive template wayback links • Articles with short description • Short description matches Wikidata • Wikipedia indefinitely semi-protected pages • Wikipedia indefinitely move-protected pages • EngvarB from January 2019 • Drugs with non-standard legal status • Chemical articles without CAS registry number • Articles without EBI source • Chemical pages without ChemSpiderID • Chemical pages without DrugBank identifier • Articles without KEGG source • Articles without InChI source • Articles without Penisilin source • Drugs missing an ATC code • Articles containing unverified chemical infoboxes • All articles with specifically marked weasel-worded phrases • Articles with specifically marked weasel-worded phrases from May 2021 • All articles with unsourced 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